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Chicago Bucket List: 10 Things to Do With Your Dog

If you come across any “Top Dog-friendly Cities in the U.S.” list, Chicago is sure to be on it. Below are fun things to do with your dog in the windy city that are sure to make doggie friends jealous (and yours, too!)

1. Cruise with your dog.

No boat? No problem. Mercury’s Canine Cruise invites pups (and their humans) for 90-minute weekend river and lake cruises. Feel the wind in your hair (and fur) while taking in the sights and learning about Chicago’s buildings and history. Dogs can comfortably sit on laps, seats or the deck. Water bowls and newspaper-lined “doggie restroom” aboard. Discount parking and prime location on Riverwalk makes it easy to extend your fun beyond the cruise.

2017: Saturdays & Sundays at 10:15am, July 8 - September 24

Image: Live Like Roo Foundation

2. Go to a baseball game with your dog.

The Chicago White Sox host two Dog Days a year, usually in May in September. Enjoy the ballpark’s drool-inducing “dog” (a brat smothering in sauteed green peppers and onions - believe us, your nose will lead you right to it) or a classic Chicago dog while enjoying America’s favorite pastime with your best bud.

2017: Wednesday, September 6

3. Frolic on the beach with your dog.

Chicago has 28 miles of lakefront shoreline along freshwater Lake Michigan. Along that shoreline you will find 24 beaches. One of which is Montrose Beach. There you will find Chicago’s first legal off-leash beach which was also named the Best Dog-Friendly Beach in the U.S. by USA Today. And perhaps some of the happiest pooches around, frolicking in the waters of Lake Michigan. A must for water-loving dogs and their people.

Go glam for a puptastic cause and bring the ultimate date - your dog! PAWS Chicago’s annual Fur Ball raises funds to support the shelter’s mission to building a no kill Chicago, providing spay/neuter services for under-resourced communities and showcasing the organization’s lifesaving success to be a model for communities to replicate around the world.

Some Chicago festivals allow dogs (typically neighborhood fests); some don’t (think Blues Fest, Taste of Chicago, etc). This particular fest has an area dedicated to your VIP - very important pet! West Fest’s Pet Fest in West Town features a charity dog wash, dog obstacle course, paw painting, pet retail booths, tie-dye dog bandana making and more. All proceeds benefit Alive Rescue and One Tail at a Time.

2017: Friday, July 7 - Sunday, July 9

Image: West Fest

7. Hike a (city) trail with your dog.

Enjoy a "paw"fect day out with your pup, meandering down Morton Arboretum's 16 miles of hiking trails during Tails on the Trails. Dogs are allowed on the trails only a few times a year, so this is special indeed! There is also an onsite pet expo, special demonstrations and adoptable dogs! Sign your pooch up for some doggy games, including the crowd-favorite peanut butter licking contest!

For a city dog-friendly “trail”, check out The 606, an abandoned rail line turned into an elevated 2.7 mile park on the northwest side.

Image: Morton Arboretum

8. Dine on the Riverwalk with your dog.

Chicago’s dog-friendly Riverwalk is one of the hottest new outdoor spaces to be in Chicago. And the perfect destination for a bite to eat outdoors! Check out Riverwalk places to nosh or sip including City Winery, Tiny Lounge, O’Brien’s Riverwalk Cafe, Island Party Hut and more.

Image: City Winery

9. Visit a brewery with your dog.

Dovetail Brewery is a local brewery in the North Center neighborhood merging continent European styles and techniques with American creativity to produce the kind of beers found in small, family-run breweries in Europe. Dogs are allowed in the taproom at Dovetail and the staff leave out bowls of water for their doggy customers. The taproom is BYOF (bring your own food). Coming soon: natural, homemade dog treats made from the leftover spent grains of the beer brewing process.

Image: Kristan Lieb / Chicago Tribune

10. Run a 5K with your dog.

Run with (or without) your pup and raise money for deserving pups! Double your feel good endorphins with some exercise and doing good. Upcoming races include: